Molecular Engineering To Enhance Reactivity and Selectivity in an Ultrafast Photoclick Reaction

Author:

Fu Youxin1ORCID,Simeth Nadja A.2ORCID,Toyoda Ryojun13ORCID,Brilmayer Robert1,Szymanski Wiktor14ORCID,Feringa Ben L.1ORCID

Affiliation:

1. Centre for Systems Chemistry, Stratingh Institute for Chemistry, Faculty for Science and Engineering University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands

2. Institute for Organic and Biomolecular Chemistry, Department of Chemistry University of Göttingen Tammannstr. 2 37077 Göttingen Germany) Cluster of Excellence “Multiscale Bioimaging: from Molecular Machines to Networks of Excitable Cells” (MBExC), University of Göttingen (Germany

3. Department of Chemistry, Graduate School of Science Tohoku University 6-3 Aramaki-Aza-Aoba, Aoba-ku Sendai 980-8578 Japan

4. Department of Radiology, Medical Imaging Center University of Groningen, University Medical Centre Groningen Hanzeplein 1 9713 GZ Groningen The Netherlands

Abstract

AbstractLight‐induced 9,10‐phenanthrenequinone‐electron‐rich alkene (PQ‐ERA) photocycloadditions are an attractive new type of photoclick reaction, featuring fast conversions and high biocompatibility. However, the tunability of the reaction was hardly investigated up to now. To this end, we explored the influence of substituents on both reaction partners and the reaction rate between the PQs and ERAs. We identified new handles for functionalization and discovered that using enamines as ERAs leads to drastically enhanced rates (>5400 times faster), high photoreaction quantum yields (ΦP, up to 65 %), and multicolor emission output as well as a high fluorescence quantum yield of the adducts (ΦF, up to 97 %). Further investigation of the photophysical and photochemical properties provided insights to design orthogonal reaction systems both in solution and on nanoparticle surfaces for ultrafast chemoselective functionalization by photoclick reactions.

Funder

European Research Council

Alexander von Humboldt-Stiftung

Ministerie van Onderwijs, Cultuur en Wetenschap

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

General Chemistry,Catalysis

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